10201. Cyclopamine

Nomenclature

CAS number: 4449-51-8
(2′R,3S,3′R,3′aS,6′S,6aS,6bS,7′aR,11aS,11bR)-1,2,3,3′a,4,4′,5′,6,6′,6a,6b,7,7′,7′a,8,11,11a,11b-Octadecahydro-3′,6′,10,11b-tetramethylspiro[9H-benzo[a]fluorene-9,2′(3′H)-furo[3,2-b]pyridin]-3-ol; 11-deoxojervine.
C27H41NO2; mol wt 411.62.
C 78.78%, H 10.04%, N 3.40%, O 7.77%.

Description and references

Teratogenic Veratrum alkaloid; causes cyclopia and other birth defects when ingested by grazing animals during gestation. Inhibits Sonic hedgehog signal transduction. Isoln from Veratrum album L. var. grandiflorum Maxima, and characterization: T. Masamune et al., Bull. Chem. Soc. Jpn. 38, 1374 (1965) DOI PubMed. Determn of cyclopian teratogenic effects in sheep: R. F. Keeler, W. Binns, Teratology 1, 5 (1968) DOI PubMed; R. F. Keeler, Lipids 13, 708 (1978) DOI PubMed. Structure studies and identification as 11-deoxojervine: idem, Phytochemistry 8, 223 (1969) DOI. ELISA determn in sheep blood: S. T. Lee et al., J. Agric. Food Chem. 51, 582 (2003) DOI PubMed. Mechanism of action study: J. K. Chen et al., Genes Dev. 16, 2743 (2002) DOI PubMed. Inhibition of Sonic hedgehog signaling in pancreas development: S. K. Kim, D. A. Melton, Proc. Natl. Acad. Sci. USA 95, 13036 (1998) DOI PubMed; in colorectal tumor cells: D. Qualtrough et al., Int. J. Cancer 110, 831 (2004) DOI PubMed. Review of biological effects and medicinal potential: W. Gaffield et al., Cell. Mol. Biol. 45, 579-588 (1999) PubMed.

Chemical structure

Properties

Crystals from methanol, mp 237-238°. [α]D23 44.2°.